Materials for organic electroluminescent devices

1. A compound of formula (I) or formula (II):

wherein

X is selected from the group consisting of C(R 1 ) 2 , Si(R 1 ) 2 , Ge(R 1 ) 2 , O, S, NR 1 , and Se;

V is, on each occurrence, identically or differently, selected from the group consisting of N or CR 2 ;

Ar 1 and Ar 2

 are, identically or differently, selected from group consisting of formulae (3) through (8):

wherein

Ar 1 and Ar 2

 are connected to the 5-membered ring of formula (I) or (II) via one group Y of one of formulae (3) through (8);

Y is C if the 5-membered ring of formula (I) or (II) is bonded to Y and is CR 3 or N if the 5-membered ring of formula (I) or (II) is not bonded to the group Y;

E is, on each occurrence, identically or differently, a divalent bridge selected from the group consisting of B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ), and P(═O)R 1 ;

W is C if a bridge E is bonded to the group W and is CR 3 or N if no bridge E is bonded to the group W;

R 1 , R 2 , and R 3

is, on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 4 , CN, Si(R 4 ) 3 , N(R 4 ) 2 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein these groups are each optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in these groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , and wherein two or more substituents R 1 , two or more substituents R 2 , or two or more substituents R 3 are optionally linked to one another so as to define a ring;

R 4 is on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R 5 , CN, Si(R 5 ) 3 , N(R 5 ) 2 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where these groups are each optionally substituted by one or more radicals R 5 and wherein one or more CH 2 groups in these groups are optionally replaced by —R 5 C═CR 5 —, —C≡C—, Si(R 5 ) 2 , C═O, C═NR 5 , —C(═O)O—, —C(═O)NR 5 —, NR 5 , P(═O)(R 5 ), —O—, —S—, SO, or SO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 5 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 5 , and wherein two or more radicals R 4 are optionally linked to one another so as to define a ring;

R 5 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F; and

a, b, c, d, e, and f

 are, on each occurrence, identically or differently, 0 or 1, with the proviso that a +b =1 or 2, c +d =1 or 2, and e +f =1 or 2, wherein when a =0, or b =0, or c =0, or d 0, or e =0, or f=0, in each case the corresponding bridge X is not present.

2. The compound of claim 1 , wherein a +b =1, c +d =1, and e +f =1 or 2.

3. The compound of claim 1 , wherein X is selected from C(R 1 ) 2 , Si(R 1 ) 2 , O, or S.

4. The compound of claim 1 , wherein E is, on each occurrence, identically or differently, a divalent bridge selected from the group consisting of C(R 1 ) 2 , Si(R 1 ) 2 , O, S, and N(R 1 ), more preferably C(R 1 ) 2 .

5. The compound of claim 1 , wherein E is C(R 1 ) 2 .

6. The compound of claim 1 , wherein V is CR 2 .

7. The compound of claim 1 , wherein

Ar 1 and Ar 2

 are, identically or differently, selected from one of formulae (3-1) through (8-3):

8. The compound of claim 1 , wherein

Ar 1 and Ar 2

 are, identically or differently, selected from one of the following formulae (3-1-1) to (8-3-2):

 wherein the dashed lines represent the bonds to the 5-membered ring of formula (I) or (II).

9. The compound of claim 1 , wherein it is a compound of formula (I) or formula (II):

wherein

X is C(R 1 ) 2 , Si(R 1 ) 2 , O, or S;

V is CR 2 ;

Ar 1 and A 2

 is, identically or differently, selected from the group consisting of formulae (3-1) through (8-3):

 wherein E is C(R 1 ) 2 and Y is C if the 5-membered ring of formula (I) or (II) is bonded to Y and CR 3 otherwise;

R 1 , R 2 , and R 3

 is on each occurrence, identically or differently, H, D, F, CN, Si(R 4 ) 3 , N(R 4 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, where these groups are each optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in these groups are optionally replaced by —C≡C—, —R 4 C═CR 4 —, Si(R 4 ) 2 , C═O, C═NR 4 ,—NR 4 —, —O—, —S—, —C(═O)O—, or —C(═O)NR 4 —, an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 4 , and wherein two radicals R 1 are optionally linked to one another so as to define a ring, two radicals R 2 are optionally linked to one another so as to define a ring, or two radicals R 3 are optionally linked to one another so as to define a ring; and

R 4 is on each occurrence, identically or differently, H, D, F, CN, Si(R 5 ) 3 , N(R 5 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, where these groups are each optionally substituted by one or more radicals R 5 and wherein one or more CH 2 groups in these groups are optionally replaced by —C≡C—, —R 5 C═CR 5 —, Si(R 5 ) 2 , C═O, C═NR 5 , —NR 5 —, —O—, —S—, —C(═O)O—, or —C(═O)NR 5 —, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 5 , and wherein two or more radicals R 4 are optionally linked to one another so as to define a ring.

10. An oligomer, polymer, or dendrimer comprising one or more compounds of claim 1 , wherein the bond(s) to the polymer, oligomer, or dendrimer are optionally localised at any desired position(s) in formula (I) or (II) which are substituted by R 1 , R 2 , or R 3 .

11. A formulation comprising at least one compound of claim 1 and at least one solvent.

12. A formulation comprising at least one polymer, oligomer, or dendrimer of claim 10 and at least one solvent.

13. An electronic device comprising at least one compound of claim 1 , wherein the electronic device is selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic light-emitting electrochemical cells, organic laser diodes, and organic electroluminescent devices.

14. The electronic device of claim 13 , wherein the electronic device is an organic electroluminescent device, wherein the organic electroluminescent device comprises an anode, a cathode, and at least one emitting layer, and wherein at least one layer of the electronic device selected from the group consisting of emitting layers, electron-transport layers, electron-injection layers, and hole-blocking layers, comprises the at least one compound.

15. The electronic device of claim 13 , wherein the electronic device comprises a compound of claim 1 , wherein the compound is a fluorescent compound and is present in an emitting layer.

16. A process for preparing a compound of claim 1 , comprising reacting a 5-membered ring boronic ester derivative and a halogenated aromatic or heteroaromatic group via a C—C Suzuki coupling reaction.